


Dress Up

by Stegosaur



Category: Teenage Mutant Ninja Turtles - All Media Types
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2018-03-27
Updated: 2018-03-27
Packaged: 2019-04-13 12:45:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,135
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14112627
Author URL: https://archiveofourown.org/users/Stegosaur/pseuds/Stegosaur
Summary: Michelangelo tries to unwind in private, by trying on some clothes.  The kind of clothes he keeps hidden under his bed.





	Dress Up

     It was so incredibly rare that Michelangelo had any privacy to himself.  Donnie was frequently left at the lair while they went on patrol so he could run experiments or do repairs, and even Raph managed to wiggle his way out of duty by ‘coincidentally’ twisting his ankle or wrist.  Of course, Leonardo was an entirely different animal to figure out on that front, as good old fearless leader always seemed to be missing except when needed.  He knew Raph and Donnie didn’t notice their leader’s absence, or didn’t care, but it drove Mikey absolutely insane, because no sooner was he ready to pull out his box-o-fun for a little intimate time, then-

     “What’s on your mind, Michelangelo?” That smug, know-it-all voice called to him from his bedroom door, sending a chill down the runt turtle’s shell.  If there’s one thing he hated more than Leo’s constant watchful eye, it was his uncanny ability to remain absolutely silent and invisible until he _wanted_ to be known.  No amount of creaky joints, loose knick-knacks in precarious positions, or even hardcore infrared tripwires ‘borrowed’ from Donnie could give him warning of Leo’s approach.  Worse yet, this time he was in a precarious spot: his fingertips were just brushing against his aforementioned toy box, but not far enough under his bed that he couldn’t feign grabbing his box of manga instead.  No, that would be too obvious, especially to Leo.  That left option C…

     “Dude! Do you ever fucking knock?” He yanked his hands back to his hips before standing upright, spinning to face his older brother.  “What do you _think_ was on my mind, huh?” He thrust his hands downward in a pointing motion, framing his flaccid cock hanging free of his slit.  If there’s one thing he knew about Leo, it was that his brother was a massive prude, and the rest of the conversation would play out accordingly.

     “Shit, Mikey! I-I-I’m sorry!” Michelangelo kept a stone-faced frustration on display, taking a few strides across the carpet towards Leonardo.  “I’ll leave you be!”

     “Damn right, you’ll leave me alone! My door was closed, and I’m not gonna tolerate any of your fucking ninja shit when I’m trying to nut!”  He thumped his fingers against Leo’s chest in a display of dominance, firmly pushing his brother back out of the doorway.  “Knock next time, asshole!” He slammed the door in Leo’s face once his brother passed the threshold, lamenting the lack of a door brace or lock like Donnie had on his lab.  Still, the clang of metal against stone would serve as an adequate warning to anyone else who may have heard, seeing as how Leo was clearly lying about going on patrol just a half-hour ago.  He braced the door with his shell instead, breathing a silent sigh of relief at the sound of Leo’s fading footsteps.  It was a rarity that he got genuinely angry with his family, which made it an absolutely underhanded trick to use it against them like this, but war on this scale demanded superb strategy.

     Once again, Michelangelo made his way back to the side of his bed, and wasted no time pulling the secret box from beneath it.  A paranoid glance over his shoulder confirmed his door was still closed, and with a flick of his wrists, he hoisted the box off the ground and on top of his wrinkled bedsheets, the cardboard flaps popping open with a coarse rasp.  He smiled giddily at the fabric within, each piece folded with the utmost care to creases and wrinkles, a mothball tossed in for extra care and protection.  See, while he suspected some of his brothers had more…complex tastes, Michelangelo had a decidedly simpler fetish, reflected by the orange silken panties topping the pile of clothes.

     Already bare of his gear, he glided in front of his body mirror and plucked the panties from the box.  Left leg first, he carefully guided the soft fabric up his thighs until it clung snugly to his posterior and hips, the cut nice and low to fit just under the sides of his plastron and shell.  A quick adjustment had his cock popped back into place within its protective slit, though not before a dribble of pre stained the panties with a dab of wetness.  Next was a black halter top he’d stolen from April, its open back and straps easily extended with a bit of sewing work to fit around his shell anatomy.  It flowed down over his chest to rise just above the panty line, a smile forming on his lips as he looked like he felt for the first time in a while: lithe, limber, and sexy as hell.  His skirt came next, a short little rah-rah affair he found in a thrift store and touched up with some sewing work.  Thanks to its clasp waist instead of an elastic band, it meant that sizing was far more important, as was his body shape; and to think, Donatello assumed he’d cut back on his sweets for ‘health reasons’.  He slipped it around his waist between the panties and the top, hooking it closed just under his shell before shaking his hips around, fluffing it out.  A black lace layer made up its bottom, while bright orange fabric contrasted its top, the two bouncing with even slight movement of its wearer.  The lace was Michelangelo’s design choice, replacing the plain white layer that originally comprised the former cheerleader skirt.

     With the main clothes in place, it was time to accessorize, starting with a pair of thigh-high silk stockings in a nice, inky black.  These were the single hardest piece to find in his size and shape, and he made sure to stock up on spares once he found them, just in case of tears.  He tucked his toes into the tip of the foot, carefully unrolling it up along the length of his leg and past the thickest point of his thigh, then repeating the same delicate procedure on his opposite leg.  Despite his decidedly feminine appearance, he found that choosing shoes were the easiest accessory of all: a pair of custom Chucks that he ordered online, black canvas with white rubber soles, orange starbursts and shoelaces accentuating the design. Those slid over his feet with ease and were hastily tied, Michelangelo casting another, increasingly nervous glance over his shoulder toward the doorway, and sighing outwardly upon seeing it still closed.  There was one more accessory left, but putting it on was his biggest risk yet.

     Hesitantly, he reached into the box and pulled out a bag from Sephora, swallowing hard at the contents within. _You can do this, Mike. It’s easy to remove, just wipe it off with the pad when you’re done._ His fingers plucked a tube of lipstick from the shallow bag and popped off its cap, gently twisting it until the rich blue tip exposed itself.  He’d not dared risk looking up guides to applying it properly online, lest he chance Donnie asking questions, but he’d also seen enough TV that he figured it wouldn’t be that hard.  Starting at the center of his bottom lip, he carefully pulled and dabbed it along his entire lip line, going from corner to corner and repeating the process up top.  The royal blue clashed nicely with his orange and black motif, but that was only part one of the process.  Next came the similarly colored eyeliner pencil, Michelangelo leaning in towards the mirror and carefully applying it to the top of his eyelids in a thin, contoured line, carefully wiping off any mistakes and blinking to make sure it looked right to him.  Satisfied, he dropped the pencil back in the bag and tossed it onto the bed, before taking a step back from the mirror.

     He looked beautiful.  Orange always was his favorite color, but the inky black stockings and lace of the rah-rah set it off wonderfully, as did the halter top.  The makeup was his latest addition, but the royal blue complimented the shade of orange he wore to great effect.  All in all, it was a alluring outfit that felt so perfectly right for him to wear, an outward reflection of his inner beauty.

     His bliss was shattered as he felt familiar fingers trickle up his thigh from behind, the digits reaching under his skirt and tugging gently at the hem of his panties.  Frozen in fear, he dared not move or speak as Leo’s other arm circled around his opposite side, index finger and thumb gripping at his chin and holding his gaze directly ahead.  “So this is what my little brother was up to, hm? Playing dress up?” The voice sounded judgmental in tone, even as Leo’s fingers indicated otherwise by pressing against his slit through the silken panties.  “No, dress up implies curiosity, experimentation.  This detail, this design…it shows confidence and planning, not mere curiosity.”  Michelangelo began to squirm half-heartedly as he was dissected by their leader, their elder, his brother, but was greeted by a tighter, almost painful grip on his chin.  “The colors compliment and contrast with perfect coordination, everything sized around our unique anatomy and proportions without compromising stylistic choices.”  The fingers pressing into his panties dug deeper, soiling them with his sticky pre even as Leo craned his head around, cold eyes staring into his own reflection and sizing him up.  “Though the makeup is new.”

     “I-I can explain-“ Michelangelo tried to plead, only to be greeted with a rough twist of his body by Leo’s hand, his brother snatching both of his wrists in his left hand and pinning them hard above Michelangelo’s head and against the stone wall of his bedroom, Leo’s other other hand keeping a hard grasp on Mikey’s chin.

     “Shut up, Michelangelo.” The voice sounded mean, disappointed, harsh, yet Leonardo’s actions continued to contradict his tone and leave Michelangelo confused at best.  Leo’s hand left his chin and thrust under his skirt once more, those thick fingers probing deeper into his slit and sliding the silky fabric around inside.  “If you did not wish to suffer the shame of embarrassment at being found out, then you had two options: first, you do not commit the act in the first place, repress your desires, and never risk being caught at all.”  Michelangelo squirmed harder now, Leo’s grip unyielding as he was pressed against the wall.  “Alternatively, you admit to it to those you risk being caught by, and deal with the consequences then and there.”

     There was a beat of silence between them, as Leo’s stony face melted into a warm smile, and the full weight of what his brother just told him sank in.  No words were spoken, only a parting of mouths as Leo pressed his lips to Michelangelo’s, forcing a heavy kiss on his compromised sibling.  Michelangelo, for his part, quickly became aroused by Leo’s sudden domination of his person, his cock dropping out of its slit and into Leonardo’s waiting fingers.  Lipstick smeared across their tongues and teeth as they passionately kissed there against the bedroom wall, the elder turtle manipulating his younger brother to a rapid and heavy climax.  Michelangelo tensed sharply and bent his knees inward as he shot his load between Leo’s fingers and into the panties, moans turning to whimpers as his brother milked him for a few strokes after his climax for good measure.  Leonardo broke the kiss while keeping Michelangelo pinned to the wall, the younger turtle panting slightly before mustering a short response.  “I love cross dressing. I can’t help it, I-“ Leo smothered him with another kiss, silencing his defense before breaking off again.

     “We’re mutants, Mike. Pretty sure societal gender norms don’t apply to us.”  Leo’s smile was warm and reassuring, his grip on Michelangelo’s wrists loosening once he was satisfied Mikey wouldn’t slump to the floor.  “Although it appears you’ll need to wash those panties of yours quite soon.  Why not get that done before Don and Raph return from their salvage trip?”  Fully released from Leo’s grip, Michelangelo watched his brother casually retreat from the wall and head toward the door, pausing to look back at him.  “Oh, and make sure you get dressed first.”  Michelangelo didn’t have time to respond before Leo disappeared from view, though the meaning of his command was quite clear: a pair of blue panties lay square on his bed, matching the same shade of his makeup just as well as they did Leo’s mask.  Orange was complimented by blue, after all.

     As Michelangelo slipped out of the soiled orange panties and used them to wipe himself clean, he couldn’t help but laugh to himself.  _Another private night spoiled by Leo’s ninja bullshit. At least he made it up to me._


End file.
